The Practice of Tactical Whimsey
- ledelstein2
- 2 days ago
- 2 min read
It's Maddy's turn......

Growing up in Montana winters, then living in Chicago and later in Minnesota, I became quite accustomed to living with ice. Recently, I was in Portland, staying three blocks from a new and different form of ICE and observed a key strategy for these times, regardless of your political stance: Apply Tactical Whimsey
While this is not a good strategy for all situations in modern times, if you are any age, you need a repertoire of responses. For tense situations that raise ire, tactical whimsey is the leverage of humor to decrease stress and tension, using the universal human appeal of gentle silliness.
The phrase “tactical whimsey” seems to have been invented by Tiffany Longworth, a technical project engineer in Portland and initially first applied effectively to motivating other engineers and technical wizards to “to read, attend, and respond to volumes of necessary information” in an organizational setting. It may have helped that Tifffany had previously been a Marine sergeant and an English teacher—but she definitely learned to harness the power of humor to “leverage fun to get stuff done.”

Portland has had a lot of attention from the Oval Office recently and been described as a “war-ravaged zone” and “on fire”. I can report with confidence that this is not accurate. But the community successfully launched a global wave of serious Tactical Whimsey. Light-hearted frogs, dancing unicorns, and naked bike riders peacefully illustrated the absurdity and danger of having heavily armed but untrained troops patrol civilians who are peacefully exercising their constitutional rights. It was and is a serious situation; but silliness helped 40,000+ people stay calm and carry on.
We all need to find fun to get through challenging times. Not The Trip We Planned is a novel where old friends use clever tactics to deliver justice--and humor to appreciate the realities of aging well. Read it, gift it, and recommend it where you can. And savor healthy silliness; it lightens the load.



Delightful and helpful